Hot Windsor Cottage Rates

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Featured Cottages in Windsor

The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington MA
Stay at this cottage in Cummington. Enjoy free Wi-Fi, private pools and a garden. Our guests praise the property condition in their reviews. Popular attractions ...
Opens in a new windowThe Clearing - Quiet - Close To Nature
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

3 out of 5
Charlemont MA
Stay at this cottage in Charlemont. Enjoy air conditioning. Popular attractions Hawley Bog Preserve and Berkshire East Ski Resort are located nearby.
Opens in a new windowHawley Home w/ Deck & Mtn Views: Swim, Ski & More!
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2 out of 5
Canaan NY
Stay at this cottage in Canaan. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Queechy Lake and Hand Hollow State Forest are located ...
Opens in a new windowCharming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
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Charming historic cottage on scenic road to Mt. Greylock

Charming historic cottage on scenic road to Mt. Greylock

Lanesboro MA
Stay at this cottage in Lanesborough. Enjoy free Wi-Fi, a garden and Netflix. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation ...
Opens in a new windowCharming historic cottage on scenic road to Mt. Greylock
Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill

3 out of 5
Windsor MA
Stay at this cottage in Windsor. Enjoy free parking, a garden and in-room fireplaces. Popular attractions Tannery Falls and Wahconah Falls State Park are located ...
Opens in a new windowMassachusetts Vacation Rental w/ Deck & Grill
Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River

3 out of 5
Huntington MA
Stay at this cottage in Huntington. Enjoy free parking, a garden and patios. Popular attractions Huntington Public Library and Pettis Field are located ...
Opens in a new windowHistoric Huntington Home - Walk to Westfield River
Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres

2 out of 5
New Lebanon NY
The price is NZ$2,937 per night from 12 Jan to 13 Jan
NZ$2,937
12 Jan - 13 Jan 2026
includes taxes & fees
Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mount Lebanon Shaker Village and New Lebanon Library are located nearby.
Opens in a new windowBerkshires farm, 30+ guests, 50 acres
Charlemont Retreat on Chickley River w/ EV Charger

Charlemont Retreat on Chickley River w/ EV Charger

3 out of 5
Charlemont MA
Stay at this cottage in Charlemont. Enjoy balconies, in-room fireplaces and air conditioning. Popular attractions Hawley Bog Preserve and Hail to the Sunrise ...
Opens in a new windowCharlemont Retreat on Chickley River w/ EV Charger
Luxury Vacation Rental in the Berkshires!

Luxury Vacation Rental in the Berkshires!

3 out of 5
Williamstown MA
Stay at this business-friendly cottage in Williamstown. Enjoy free parking, patios and in-room fireplaces. Popular attractions Colonial Plaza and Williams College ...
Opens in a new windowLuxury Vacation Rental in the Berkshires!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windsor Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Windsor will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Windsor definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Windsor, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Windsor Cottages essential information

Accommodation
74 Cottages
Lowest Price
NZ$144
Highest Price
NZ$2,937
Popular accommodation
The Clearing - Quiet - Close To Nature, Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Charming historic cottage on scenic road to Mt. Greylock, Massachusetts Vacation Rental w/ Deck & Grill, Historic Huntington Home - Walk to Westfield River, Berkshires farm, 30+ guests, 50 acres, Charlemont Retreat on Chickley River w/ EV Charger, Luxury Vacation Rental in the Berkshires!

Top trending hotels in Windsor

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NZ$219 per night from 15 Dec to 16 Dec
NZ$219
15 Dec - 16 Dec
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 15 Dec to 16 Dec
NZ$379
15 Dec - 16 Dec
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is NZ$178 per night from 17 Dec to 18 Dec
NZ$178
17 Dec - 18 Dec
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$144 per night from 24 Dec to 25 Dec
NZ$144
24 Dec - 25 Dec
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Don't see what you're looking for?
See all available properties in Windsor
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.